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As early as January 1935, Pan American Airways had signified to the US Bureau of Air Commerce its wish to establish a transatlantic service and, the airline wanted a new aircraft for the route.

Boeing submitted a successful tender to the Pan American specification and a contract for six Boeing Model 314 flying-boats was signed on 21 July 1936. They used features of the XB-15 heavy bomber, adapting the wing and horizontal tail surfaces for its 37421kg gross weight flying-boat, which could accommodate a crew of 8 and up to 74 passengers in four separate cabins. The engines 1119kW Wright GR-2600 Double Cyclones which gave the machine a maximum speed of 311km/h. The fuel capacity of 15898 litres giving a maximum range of 5633km. Some of the fuel was stored in the stabilising sponsons, which also served as loading platforms.

The first Boeing 314 made its maiden flight on 7 June 1939, this original version having a single fin and rudder, later replaced by twin tail surfaces to improve directional stability. These proved to be inadequate, and the original centreline fin was restored, without a movable rudder.

The aircraft was awarded Approved Type Certificate No. 704 and entered transatlantic airmail service on 20 May 1939. PAA Boeing 314 ‘Yankee Clipper’ flew by way of the Azores to Spain and then on to Southampton. On June 17 ‘Atlantic Clipper’ made first passenger crossing, carrying reporters and airline officials. Regular passenger service commenced on 28 June 1939, when ‘Dixie Clipper’ carried twenty-two paying passengers. One passenger having booked his seat in 1931. At that time the Model 314 was the largest production airliner in regular passenger service.

Known as “California Clippers” they operated over the South Pacific Ocean routes for Pan American Airlines. One such “California Clipper” flew from Los Angeles Harbor to Auckland, New Zealand, an 8,000-mile, 50-hour route with night layovers at Honolulu, Canton Island, and Noumea, New Caledonia. On two decks—an upper or control deck and a passenger deck—there were accommodations for a crew of 11 and 68 passengers or 36 sleeping passengers. The passenger deck was divided into nine sections, including a lounge, six separate passenger compartments, a specially furnished deluxe compartment, a galley and restrooms.

Pan American ordered another six aircraft which were designated Model 314A, improved by the installation of 1193kW Double Cyclones with larger-diameter propellers, and additional 4542 litres of fuel capacity, and a revised interior. The first Model 314A flew on 20 March 1941 and delivery was complete by 20 January 1942. Five of the original order were retrospectively converted to Model 314A standard in 1942. Three of the repeat order were sold, before delivery, to BOAC for transatlantic service and operation on the Foynes-Lagos sector of the wartime 'Horseshoe Route'. The three Boeing 314As, G-AGBZ Bristol, G-AGCA Berwick, and G-AGCB Bangor, with fuel capacity of 5,448 US gallons giving a range of over 3,600 miles, were acquired by the British Government and delivered new from Boeing's Seattle factory specifically to provide the UK-West Africa 'lifeline'. The three Boeings commenced operation UK-West Africa in May 1941. It transpired that a valuable, albeit irregular, trans-Atlantic service was an incidental development due to the necessity for them to return to their Baltimore base for certain overhauls after every 120 hours flying, and Atlantic flights were therefore interpolated into the schedules to permit this to happen. BOAC operated its last B.314A on January 17, 1948.

Of Pan American's nine Model 314/ 314As, four were requisitioned by Army Transport Command and given the military designation C-98. They were little used, however, and in November 1942 one was returned to the airline. The other three were transferred to the US Navy to join two acquired direct from Pan American; the airline provided crews for the US Navy's B-314 operations and the aircraft were partially camouflaged but operated with civil registrations.

BOAC and Pan American terminated Boeing Model 314 services in 1946 and the surviving aircraft were sold to American charter airlines Clippers were in service with distinguishable names from 1939 through 1951 and were represented as the Honolulu Clipper, Cape Town Clipper, Anzac Clipper, Pacific Clipper, American Clipper, Yankee Clipper, California Clipper and the Atlantic Clipper - all operated by Pan Am.Only 12 were ever built.